Refers to American upper-middle-class culture, where certain looks, behaviors, and hobbies are valued. His preppy way of dressing showed his East Coast roots.
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Social Implications
Can imply the person is not only stylish but also has a socio-economic status associated with private education. She embraced the preppy lifestyle after her Ivy League admission.
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Subtle Disapproval
Sometimes used subtly or sarcastically to critique someone for being too conventional or materialistic. They chuckled at his preppy name-brand sweater vest.